Triazine substances for textile treatment



Patented Se t. 30, 1952 Robert H. Wils asslgnorvto This invention relates -to-enew substar ices ior textile- -ti'eatrnent andinmarticiilar it relates to a process for the manufacture of new substances ixsefu'l'fo'r producing a whitening eiiect on textile materials.

rials certain stilbene derivatives'g such as for exsimple 4 4 -'diam'inostilhene-2 2'-disulphonic acid [and the corresponding. acylamino derivatives, there are obtained textile materials which fluoresce in uitraviolet light andwhich accordingly h e; attr t teiwh teasneam c v- I Also in the specification of Unitedi gtates application Serial No. 381,856 vested in the Alien Property Custodian and published May, 11, 1943,- it was proposed to treatftextile materials with colourless or slightly-coloured-z stilbene derivatives particularly with-suchqstilbene derivatives aside not contain a freemrnino group but which do: contain at least-one l":3:5-triazine nucleus. It was proposed to prepare such compoundsby causing 1:3:5-triazyl' chloride dissolved in ace- ;3) .5- TREATMENT? on. B a kietiMax l V La he :unvention; 1th

R'TEXTILE- I host I H U i. BWWRE GSWI Q more alkyl radicals and/or one radical selected 7 7 v I v p y 1'; from the class fcomprising OH, OMe,

is---known" that by applying to textile imateample aniline, m.-toluidine, p-xyhdmmamam-inO- 10 acetanilide and, monoethanolamine.

The invention 'is'" illustrated but not limited by I v:acid prepared; aszdescribedibelow;t1szfispartshi0.2 2 ;mol) pf: aniline; areadded; The mixtureris heated at 502 G5: and :caustic :soda 4Ltimeassrequiredto make;and-:maintaindzMmus- 1 ere Mayihesmentiened,foraex- ,addedrfromgtime to tone .toreact-,withian .,aqueou s, solution .pf the --I:pension :neutral -ato Delta: test paper'ripapendmsodium salt of diaminostilbenedi'sulph nic acid '1:pregnatedrzwith'ggfi-zdsdinitrobenzene-eazoitenaphat about 0-5 C. After the reactioiifin'which 2.5-;thol13:.6=disu1phonic;acid)v. The reaction'cislccmthe solution had been maintained essentially neupleteirwhen'.I10ff -Ifit y dfl p 531118 itral, was-complete, the amine mr phenolg v(with nztakes;aboutonerhourtaslsmarts imzmolwoitediwasdboiledi order OaS8 POn.if,.any residual t az se nuclei.

None-tof the compounds mentioned in the above specification for use in the treatmentgof textile materials contains a dimethylaminoc on morpholino groupaattached to a tria'zine'nucleus.

I have now foundthat the 4:4'-di-triazy'11 diaminostilbene mgf-disu1ph0nic acid cbmpounds containing dimethylaminoor morpholi no groups attached to theltriazi'ne nuclei, have awwhitening effect on textiles superior to that obtained, with thepreviously known derivatives ocazy-dia md stilbene-2:2'-disulphonic acid.

According to my invention therefore I pro- :vide'-'-'a* process for the vinanufaotmre r new subistances'ror \textile treatmenty'whicm comprises "*"greactlng two molecular proportions oi-myanuric ichloridewith, in any order, one melcular pro- ?portion of 4 4' -diaminostilbene-2 :2-disu lphonic acid or a salt"thereoi, two molecular proportions it dimethylamine,-or=*morpholino and tjvo mo methylamine are now added, and the is salt is precipitated by adding 400 parts of sodium chloride. It "is filtered ofi and dried at 60 C. I

The productisa pale yellow solid. 1

Thegsusp'ension of 'l'l parts of the disodium salt of 414'-biS-(2Z4-diCh10lO-1i3I5-7t1i9lZy1. (6) )-diamino'stilbene-Z:2'-disulphonie" acid used in the above example is prepared. as follows::

8 parts of caustic soda are"'added"to a stirred 3 1mixture -J0fw 37; parts akorlezmolir ofriqz find-lamina- 40 water. The clear solution so obtained is added to a suspension of cyanuric chloride (obtained by adding a-solution of 36.8 parts- (0:2 mol) of cyanuric chloride-1n 92 parts of acetone to- 1600 parts of water) at 20-25 C. in 30 minutes. The

*part'sof- 10% caustic soda eluthatithe -iinal mixture is only very slightly acid to Qongo reldtest paper.

"'Emmpzea Instead of the 18.6 parts of aniline used in Example 2, 21.4 parts or n-toluidine (0.2 incl) are used, The disodium salt-'produced is azpale yellow powder. 1 o =1; 5 5

Example 3 4. A compound represented by the formula instead of the 18.6 partsof aniline used in Exsole 1 ample 2, 30.0 parts of p-amino-acetanilide are used. The disodium salt produced is a pale yelon:

To a suspension of 71.0'parts (0.1 mol) of the disodium salt of 4:4'-bis-(2:4-d1chlor0-lz'3'z5- triazyl (6) diaminostilbene-z 2;2'-'--disulphonic j wh ein;A;i lkyl' roup, acid 18.6 parts (0.211101) of aniline are3'a'olded'.hv 5. A-compound represented by the formula The mixture is heated at 59-? (Land caustic soda so H x I v and maintain the suspension neutral iton Delta' test paper (paper impregnated with '2:4-'dinitrobenzene-azo-l -naphthole3 6-.disu1ph0nic': v acid) I The reaction is complete whenno further acidity develops. This takes about one hour 3fl. 8 parts (0.4 mol) of morpholine are now added, and the 0" mixture is heated at 95 -100 C. for 5 hours. The i I me iumsm is precipitated Wedding-400' parts whewfimfiis a 3% gb of sodium'chloride; Itis'filtredofi and' drie'd at I 9 1 1 1 Y 6Q-C" -"I'heproduct is apalfe yellowsolid eeaw i n Insteadof-the 18.6 pa'rts of aniline used in Example 14,521.4133113'5 of-m-toluidine (Oz-moi) are use'd. Thfdiso'dium saltproduced is a pale yelis added from time to ti eia s requlred to" make i the formula "i -low powde'n i 0 Y v V "weihereinAi'san allty wzrfi l 'f I v 1 -'.Lnstead.ofvtl 1e 18.6.partsof aniline used in Ex- 7 A i-w m g" gen z e by the ample 4;, 30.0 parts of p-amino-acetanillde are used. The disodiumsalt produced is a pale yel low powder. 5" Ii I I claimfm .c .135; ls-Process forthemanufacture of new textile whitening agents which comprises reacting two v 1 molecular proportions of cyanuric chloride" with z lone molecular proportion of a substance from *5 thigrouprcbnsisting of 4:4! -diaminostilbene'-2:2'- =.;disu1phonic: acid andesalts thereof, two molecular proportions; of an amino 'compoundfrom the grou'p consisting of 'dimethylainine and mor- 'pholine and two molecular proportions of an amino'compound from the group consisting of w Y ,alkylfamino' and monocycli'c aryl amino com- :2; A compound represented by the formula from';the*-group consisting of s j den Cm v whom} and; 0- r J V t C IQ 13- ,i' iw e ed mini-the gifoupscon- Esi stingjoialkyl and monocycliq 8- 371 radicals;

wherein A is an aryl; group v 5 11. A new whitening agent represented by the 7 REFERENCES CITED formula The following references are of record in the SOSH file of this patent: 1 5 UNITED STATES PATENTS j (IFNH CH: Number Name Date )5 N 2,171,427 Eggert Aug, 29, 1939 g I 2,235,480 Graenacher Mar. 18, 1941 gm 3 7 2,376,743 Wendt May 22, 1945 2 10 OTHER REFERENCES ROBERT WILSON Alien Prop. Custodian Publication Ser. No.

381,856, published May 11, 1943. 

2. A COMPOUND REPRESENTED BY THE FORMULA 